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New compound in sulfonyl ureas, and medicine use

A kind of compound and drug technology, applied in the field of new sulfonylurea compound and its medical use

Inactive Publication Date: 2007-12-26
唐仲雄 +2
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The compounds involved in the present invention have not been reported in the literature so far

Method used

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  • New compound in sulfonyl ureas, and medicine use
  • New compound in sulfonyl ureas, and medicine use
  • New compound in sulfonyl ureas, and medicine use

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0024] Preparation of 1-{4-[2-(1-ethyl-2,3-dioxopiperazine-4-carboxamido)ethyl]benzenesulfonyl}-3-cyclohexylurea (code PHN)

[0025] Put 1.84 grams of 4-[2-(1-ethyl-2,3-dioxopiperazine-4-formamido)-ethyl]benzenesulfonamide, 30ml of anhydrous acetonitrile, and 1.38 grams of anhydrous potassium carbonate In a 100ml round bottom flask, heat to reflux on an oil bath and stir for 1h. Then slowly add 0.81 g of cyclohexyl isocyanate in acetonitrile solution dropwise. After the addition, continue to stir and reflux for 6 hours, then cool and filter. The filter cake was dissolved with 30 ml of ice water, filtered, and the filtrate was acidified to pH 1 with hydrochloric acid, and crude PHN was precipitated. The crude product was recrystallized from dilute methanol to obtain 1.76 g of white solid. Yield 68.22%.

[0026] 1 H NMR (400MHz, DMSO-d 6 )

[0027] δ=1.058 (triplet, J=7.28Hz, 3H); 1.114 (multiplet, J=9.80Hz, 4H); 1.468 (multiplet, 2H); 1.566 (multiplet, J=3.36Hz, 4H); 2.88...

Embodiment 2

[0032] 1-{4-[2-(1-Ethyl-2,3-dioxopiperazine-4-carboxamido)ethyl]benzenesulfonyl}-3-(trans-4-methylcyclohexyl) Preparation of urea (code PJN)

[0033] PJN was prepared according to Example 1. Yield 60.22%.

[0034] PJN molecular formula and molecular weight C 23 h 33 N 5 o 6 S(507.6)

[0035] 1 H NMR (400MHz, DMSO-d 6 )

[0036] δ=0.815 (doublet, J=6.44Hz, 3H); 0.870 (triplet, J=12.32Hz, 3H); 1.072 (multiplet, J=3.08Hz, 4H); 1.238 (multiplet, J=5.32Hz , 1H); 1.583 (doublet, J=12.60Hz, 2H); 1.668 (doublet, J=12.04Hz, 2H); 2.725 (triplet, J=7.00Hz, 2H); 2.887 (triplet, J=7.00Hz, 2H); 7.00Hz, 2H); 3.231 (complex peak, 1H); 3.493 (triplet, J=7.00Hz, 2H); 3.533 (quartet, J=5.88Hz, 2H); 3.904 (complex peak, 2H); 6.279 (doublet, J=7.28Hz, 1H); 7.453 (doublet, J=8.12Hz, 2H); 7.805 (doublet, J=8.40Hz, 2H); 8.905 (triplet, J=5.60Hz, 1H) ; 10.336 (singlet, 1H).

[0037] MS(FAB): m / z=508.3[MH]+

Embodiment 3

[0039] Preparation of 1-{4-[2-(1-acetyl-2-oxo-imidazolidinone-3-carboxamido)ethyl]benzenesulfonyl}-3-phenylethylurea (code MBN)

[0040] 1.77 grams (0.005mol) of 4-[2-(1-acetyl-2-oxo-imidazolidinone-3-carboxamido)-ethyl]benzenesulfonamide, 30ml of anhydrous acetone, 1.38 grams (0.01mol ) Anhydrous potassium carbonate was placed in a 100ml round bottom flask, heated to reflux on an oil bath, and stirred for 1h. Then slowly add 0.81 g (0.0055 mol) of an acetone solution of phenylethyl isocyanate dropwise, after the addition, continue to stir and reflux for 6 hours, cool, filter, dissolve the filter cake with 30 ml of ice water, filter, and use hydrochloric acid to dissolve the filter cake Acidify to pH 1, collect the solid by filtration, and dry to obtain crude MBN, which is recrystallized from dilute methanol to obtain 1.68 g of white solid. Yield 66.93%.

[0041] 1 H NMR (400MHz, DMSO-d 6 )

[0042]δ=2.623 (triplet, J=7.28Hz, 2H); 2.750 (triplet, J=7.00Hz, 2H); 2.837 (tri...

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Abstract

This invention relates to a novel sulfonylurea compound or its pharmaceutical salt, their preparation method and pharmaceutical application. The novel sulfonylurea compound or its pharmaceutical salt can be used in drugs for preventing and treating diabetes or other diseases. The compound can be manufactured into oral liquids, injections and external use preparations.

Description

Field of invention: [0001] The present invention relates to a novel sulfonylurea compound and its medical use, especially the use in preparing medicines for treating or preventing diabetes or other diseases. Background technique [0002] Diabetes is a global clinical common metabolic and chronic disease. In recent years, with the development of economy and the change of people's diet structure, the prevalence rate is increasing rapidly all over the world. According to statistics, the total number of patients in the world can reach more than 120 million, and it is estimated that there are more than 30 million in my country, most of which are non-insulin-dependent (type II) diabetes. It can be seen that diabetes has become another serious disease that seriously endangers people's health after cardiovascular and tumors. [0003] Diabetes has a long course of disease and improper treatment often leads to complications, such as chronic vascular complications (including cerebrov...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D241/08C07D233/38C07C311/57A61K31/145A61K31/495A61K31/4166A61P3/10
Inventor 唐仲雄吴祖泽孙庄蓉王国光
Owner 唐仲雄
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